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United States Patent Office Patented Apr 3,245,916 United States Patent Office Patented Apr. 12, 1966 2 is to provide a stabilized epoxy resin curing agent that is 3,245,916 liquid at ambient temperatures. Still another object of STABLE ANHYDRDE MIXTURES this invention is to provide a process for stabilizing low Marvin 2. Woskow, Houston, Tex., assignor to Petro melting mixtures of polybasic acid anhydrides. Another Tex Chemical Corporation, Houston, Tex., a corpora object is to provide an improved process for curing epoxy tion of Delaware resins with stabilized low-melting or eutectic mixtures of No Drawing. Filed Nov. 8, 1962, Ser. No. 236,437 polybasic acid anhydrides. Other objects of this inven 8 Claims. (C. 252-182) tion will be apparent from the disclosure which follows. This invention relates to stabilized low-melting or eutec It was unexpectedly found that these objects are ac tic mixtures of acid anhydrides. O complished by adding to a mixture of two or more poly Liquid epoxy resins are produced by combining bis basic acid anhydrides an organic compound containing at phenol-A 2,2-bis(p-hydroxyphenyl)propanel with epi least one carbinol group chlorohydrin in the presence of sodium hydroxide which may then be hardened or cured into tough, hard, thermoset solids by adding thereto specific amounts of acid anhy 5 --OH) drides. Epoxy resins and the curing thereof are described A variety of carbinol-containing compounds, such as in "Epoxy Resins Their Application and Technology,” aliphatic, aromatic, and cyclic mono- and polyhydric Lee and Neville, McGraw-Hill Book Co., Inc. (1957), alcohols and mixtures thereof may be utilized in formulat with particular reference to pages 3-14 and 115-139. ing stabilized liquid mixtures of polybasic acid anhydrides. Typical linear and cyclic acid anhydrides that may be 20 Specific examples of such compounds include saturated employed in curing or hardening epoxy resins generally aliphatic monohydric alcohols such as, methyl alcohol, contain from about 4 to 25 carbon atoms per molecule ethyl alcohol, n-propyl alcohol, isopropyl alcohol, isobutyl of acid anhydride. Examples of such anhydrides include alcohol, tert-butyl alcohol and the like; ethylenically un aliphatic linear monobasic acid anhydrides such as pro Saturated aliphatic monohydric alcohols such as allyl pionic anhydride, acetic anhydride, acetyl butyrate and 25 alcohol and the like; aromatic alcohols such as benzyl the like; aromatic linear monobasic acid anhydrides such alcohol, O-phenylethyl alcohol, 6-phenylethyl alcohol, cin as benzoic anhydride and the like; aliphatic cyclic poly namyl alcohol, triphenyl carbinol, salicyl alcohol, and the basic acid anhydrides such as maleic anhydride, succinic like; Saturated aliphatic polyhydric alcohols, such as ethyl anhydride, and the like, aromatic cyclic polybasic acid ene glycol, diethylene glycol, propylene glycol, 1,2- anhydrides such as trimellitic anhydride, pyromellitic 30 butanediol, pentamethylene glycol, glycerol, erythritol, anhydride, phthalic anhydride and the like. A preferred Xylitol, Sorbitol and the like; cyclic polyhydric alcohols, group of cyclic acid anhydrides contain 4 to 8 carbon Such as pentahydroxycyclohexane, hexahydroxycyclo atoms; however, such anhydrides may contain additional hexane, and the like. Various derivatives of aliphatic carbon atoms attached to the cyclic member. Certain mono- and polyhydric alcohols, such as the halogen cyclic dibasic acid anhydrides derived from maleic anhy derivatives, including glyceryl monochlorohydrin, have dride are of particular importance and include for ex also been found to be useful. Alcohols containing 1 to ample, dodecenylsuccinic anhydride, hexahydrophthalic 12 carbon atoms and 1 to 8 hydroxyl groups are generally anhydride, tetrahydrophthalic anhydride, nonenylsuccinic used. Saturated aliphatic alcohols containing 1 to 6 car anhydride, isatoic anhydride, chlorendic anhydride, and bon atoms and 1 to 5 hydroxyl groups are preferred. the like. Most of the above anhydrides are solid at room 40 For example, the polyhydric alcohols such as ethylene temperature and have the disadvantage of being only glycol and propylene glycol and the monohydric alcohols partially soluble in liquid epoxy resins at room tempera such as methanol and isopropanol are generally preferred ture. To insure proper mixing of the ingredients and to for commercial use. avoid precipitation of the polybasic acid anhydrides during The amount of alcohol that is required to stabilize a the curing and casting process, an elevated temperature liquid mixture of acid anhydrides may be varied over a must be utilized throughout the operation to maintain the Wide range. Generally good results have been obtained ingredients in liquid phase. Operation at these elevated by adding to the acid anhydride mixture a mono- or poly temperatures is cumbersome and creates undesired opera hydric alcohol in an amount above 0.001 percent to about tional limitations and may affect the physical properties 10 percent by weight of the total anhydride mixture, al of the cured epoxy resin. 50 though larger amounts, while not necessary, may be used. While the problems associated with the use of solid A mono- or polyhydric alcohol in an amount between anhydrides may be avoided by using liquid acid anhy about 0.02 to 4 percent by weight of the total anhydride drides or low-melting or eutectic mixtures of specific acid mixture is preferred and excellent results obtained. anhydrides, it has been noted that liquid acid anhydrides, Where the stabilized liquid anhydride is exposed to the and in particular the low-melting or eutectic mixtures of 55 atmosphere, in handling or storage, larger quantities of the polybasic acid anhydrides decompose upon standing and stabilizing alcohol may be required. Since the alcohols form a precipitous substance. In some instances decom may be consumed, in part, while functioning as stabilizing position was noted as soon as the individual molten anhy or inhibiting agents, the amount of alcohol initially drides were combined and cooled. Although the nature introduced depends on the length of time as well as the of the decomposition of the anhydride mixture is not fully 60 conditions under which the anhydrides are to be stored. understood, the precipitate that develops seriously hinders The low-melting or eutectic anhydride mixture is gen the use of low-melting or eutectic mixtures of polybasic erally composed of at least two acid anhydrides although acid anhydrides. more may be used. For example, a 100 part mixture It is, therefore, an object of this invention to provide containing between 10 to 50 parts of maleic anhydride and stabilized low-melting mixtures of polybasic acid anhy 50 to 90 parts hexahydrophthalic anhydride will possess drides which resist decomposition. Another object of this invention is to provide stabilized eutectic mixtures of a melting point below 23° C. A 100 part mixture con cyclic dibasic acid anhydrides. A further object of this taining between 10 to 27 parts of tetrahydrophthalic anhy. invention is to provide stabilized mixtures of maleic anhy dride and 73 to 90 parts hexahydrophthalic anhydride dride and anhydride derivatives thereof, particularly eutec 70 will also possess a melting point of below 23° C. Various tic mixtures that are liquid at temperatures from about other low-melting anhydride combinations may be em 0° C. to 30° C. A still further object of this invention ployed, for example, chlorendic and hexahydrophthalic 3,245,916 3 4.3. anhydride; propionic acid and pyromellitic anhydride; small amounts of a mono- or polyhydric alcohol or mix maleic and tetrahydrophthalic anhydride and the like. tures thereof to these anhydride mixtures produced a The procedure for formulating stabilized liquid poly stabilized low-melting or eutectic anhydride mixture. basic acid anhydride mixtures will usually consist in first Similarly, when a liquid mixture of about 20 to 40 parts melting the polybasic acid anhydrides and adding thereto of 1,4,5,6,7,7-hexachlorobicyclic-(2,2,1)-5-heptane-2,3-di the desired amount of stabilizing alcohol compound. carboxylic anhydride, about 60 to 80 parts of hexahy The mixture during or after mixing, is heated to a tem drophthalic anhydride, and about 2 weight percent of perature above 80° C., and preferably to a temperature ethylene glycol are prepared and the sample heated to between about 90° C. and 150° C. The alcohol-anhy about 150° C. and maintained at that temperature for dride mixture is held at this elevated temperature until all O about 5 minutes before being capped and cooled, after visible traces of gaseous impurities have been evolved. a three-month period this stabilized low-melting mixture Usually five to ten minutes at the elevated temperature is shows no visible signs of decomposition. sufficient, although a longer period of time may be used. It is also advisable, although it is not essential, to purge Example 3 the vapor space above the liquid anhydride mixture dur In order to demonstrate the curing characteristics of ing the heating and cooling process with a dry inert gas the stabilized anhydride mixtures with epoxy resins, or material substantially inert to the ingredients. The twenty gallons of a stabilized low-melting anhydride mix stabilized anhydride mixture may also be maintained ture was prepared as follows: 143.5 pounds of hexa under a dry inert atmosphere while in transit or storage. hydrophthalic anhydride, 21 pounds of tetrahydrophthalic Dry inert materials that may be suitably employed in 20 anhydride and 2.25 pounds of ethylene glycol were placed clude such materials as methane, carbon dioxide, helium, in a 30-gallon, glass-lined steam-jacketed, Pfaudler auto nitrogen, and the like. clave. The anhydride-alcohol mixture was thoroughly The effect of adding a specified amount of a mono- or mixed by a motor-driven, propeller-type mixing device polyhydric alcohol to a low-melting or eutectic mixture and heated until a temperature of about 150° C. was of polybasic anhydrides is demonstrated in the following obtained. During the heating process a slow stream of examples.
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