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Patented Mar. 15, 1960 Dihydroxybenzophenone, Bis(4

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Patented Mar. 15, 1960 Dihydroxybenzophenone, Bis(4 2,928,811 Patented Mar. 15, 1960 2 2,928,811 Glycidyl polyethers with which this invention is con-' EPOXIDE RESIN-AMIDE COMPOSITIONS cerned are now. well known and need not. be discussed at William J. Belanger, Louisville, Ky., assignor to Devoed: length herein. The most useful of these epoxide; resins Raynolds Company, inc, a-corporation of New York is made from thereaction of a, polyhydric phenol with» No Drawing. Application November 18, 1957 epihalohydrin or glycerol dihalohydrin and a su?icient ' Serial No. 696,951 amount of a caustic alkali to combine with the halogen 4 Claims. ((1260-47) of the halohydrin. Products resulting from the reaction, This invention relates to heat curable compositions of of a polyhydric phenol with, epichlorhydrinvor glycerol matter particularly suitable for the formation of- castings, dichlorhydrin are monomeric or straight chain‘polymeric, pottings, and thin ?lms as used in coatings, adhesives 10 products. characterized by the presence of more than one, and the, like. More particularly’. the invention is con epoxide group, i.e., a 1,2-epoxy equivalency, greater than cerned with compounding and reacting glycidyl poly one. Dihydric phenols that can be used for this purpose ethers with selected amides to form intermediates having include bisphenol, resorcinol, catechol, hydroquinone, epoxide groups as well as valuable insoluble, infusible methyl resorcinol, 2,2-bis(4-hydroxyphenyl'),butane, 4,4’ cured products. 15 dihydroxybenzophenone, bis(4-hydroxyphenyl)ethane, It is known to use amides as curing agents for glycidyl and 1,5-dihydroxy naphthalene, The preparation of polyethers, particularly amides which are believed to polyepoxides from polyhydric phenols and epihalohydrin decompose. However, reactions involving glycidyl poly is described in US. Patents 2,467,171, 2,538,072, ethers and these amides. are quite sluggish. Representa 2,582,985,, 2,615,007. and. 2,698,315, the proportion. of. tive amides of this type are dicyandiamide, which is a 20 halohydrinI to dihydric phenol being. at least about, 71.2, dimer of cyanamide, and benzoguanamine, derived from to 1, up toaroundlO to 1_. V '1; melamine, which is an amide of cyanuric acid. Mel Higher melting point resinsv are made from the reaction amine is 2,4,6-triamino-1,3,5-triazine, whereas the amide of such resins with a further. amount; of-dihydric- phenol benzoguanamine is 4,6-diamino-2-phenyl-1,3,5-triazine. less than that equivalent to the epoxide content of the When these amides are used with glycidyl polyethers, 25 resin, as set forth in U.S. Patent 2,615,008. Halohydrins even if a solvent is‘employed, the reaction is too slow for can be further exempli?ed by 3-chloro-1,2-epoxy butane, many purposes. In accordance with this invention, how 3-bromo-1,2-epoxy hexane, 3-chloro_-1,2-epoxy octane ever, glycidyl polyethers are reacted with dicyandiamide and the like. Another group of glycidylv polyethers is or benzoguanamine in the presence of special accelera~ produced by the reaction of a polyhydric alcohol with tors. Ithasheen found that quaternary ammonium salts 30 epichlorhydrin or glycerol dichlorhydrin as disclosed in are capable of accelerating or activating the reaction Zech patent US. 2,581,464. While the invention, is ap between glycidyl polyethers; and these amides. When plicable to epoxides generally, preferred polyepoxid'es are benzoguanamine. or dicyandiamide is used in combina glycidyl polyethers of aromatic polyhydric compounds tion with these activators, they display surprisingly in having Weights per epoxide group of- 180 to 2000.‘ creased activity as curing agents for glycidyl polyethers. 35 In carrying out the’ process of this invention, the glyci The invention thus provides: a process; for curing, glycidyl dyl polyether and benzoguanamine or dicyandiamide are polyetherswhich- includes mixing and reacting the glycidyl heated; together until a homogeneous composition is polyether, benzoguanamine or dicyandiamide, and, as an formed, generally at a temperature in the range of; 140° activator for the amide, a quaternary ammonium salt. C. to 180°- C., and ‘then the quaternary ammonium salt Quaternary ammonium salts are those salts of strong, 40 is added. No particular difficulties are encountered; ex and weak. organic and inorganic acids. Included are cept those due to the limited-'solubilities of'dicyandiamide such acids asacetic, oxalic, formic, furnaric, benzoic, and and benzoguanamine. Accordingly, when ?lms of inter“ maleic, as well as hydrochloric, phosphoric, sulfuric, and mediate epoxide resins, to be described, are‘preparem'it hydrobromie acids, having pK values not exceeding’ six. will be desirable to use a, solvent». In the case of castings, These quaternary ammonium salts are well known tetra no solvent- is employed; Whena solvent is used,v astrong alkyl, aryl trialkyl and: alkar-yl trialkyl ammonium salts 45 solvent is necessary because of‘ the solubility character of acids having pK valuesnot exceeding six, wherein. the istics of both of the amides, as well as the glycidyl poly aryl, alkaryl and alkyl- substituents each have no more ether. In other words, a polar solvent is used rather than eight carbon atoms. Typical quaternary ammonium than a non-polar solvent, particularly ethers and ketones, salts. are benzyltrimethyl. ammonium acetate, benzyltri esters being less. desirahlebecause of their possible. teas; ethyl ammonium formate, di(phenyltrimethyl)ammo 50 tion with the amide. For this purpose, suitable solvents nium maleate, di(tolyl trimethyl ammonium)fumarate, are ethers such as. “Dioxane” (glycol ethylene ether)’, the benyltrimethyl ammonium ethyl hexoate, di(benzyltri “Cellosolves” such as ethyl “Cellosolve” (2-ethoxyethan~ methyl ammonium)oxalate, di(benzyltrimethy1 ammo ol), butylmcellosolve” (butoxy ethanol), and “Cello nium)tartarate, benzyltrimethyl ammonium lactate, ethyl solve” acetate (Z-ethoxyet-hanol acetate), ~etc.; ketones ene'bisltrimethyl ammonium acetate), .octyl trirnethyl 55 such as acetone, methyl ethyl ketone, methyl isobutyl ammonium benzoate', benzyltributyl ammonium acetate, ketone, diisobutyl ‘ketone, etc.; and mixtures of ketone benzyltrimethyl ammonium chloride, benzyltrimethyl solvents and ether solvents with aromatic hydrocarbon ammonium phosphate, trimethyl benzyl ammonium sul solvents, such as xylene, toluene, benzene, etc. ‘ phates, benzyltriethyl ammonium chloride, tributyl benzyl Of course, when a solvent is used, the reaction tem~ ammonium chloride, tripropyl benzyl ammonium chlo perature cannot be above the boiling point of the solvent‘. ride, tolyl trimethyl ammonium chloride, octyl trimethyl In general, the amide and the glycidyl polyether are're ammonium bromide, ethylene bis(trimethyl ammonium acted at temperatures of from 100° C. to 150"~ Q,’ a bromide), ethyl pyridine chloride, etc., preferred salts period of from two to sixteen hours being recommended being quaternary ammonium halides. Also intended are for cures. If it is deemed desirable to increase the rate ion exchange resins containing quaternary ammonium of reaction, it will be necessary to use a higher boiling salts of strong acids. The quaternary ammonium salts point solvent so that the reaction can. be carried out at a are utilized in amounts varying from 0.1 percent to 10 higher temperature.‘ 7 j v ~ percent by weight oflthe glycidyl polyether-amide com The following examples are illustrative. of. adesired position, and more preferably in amounts varying from method of preparing the polyepoxides forming an aspect 0.1 percent to 2 percent by weight of the amide-polyether 70 of this invention. It is understood, of course, thatthe composition. > procedures are exemplary only» and that variations will 2,928,81 1 3 occur'to' those skilled in the art. The glycidyl polyethers EXAMPLE 18 employed in the following examples are prepared in the manner described in US. Patents 2,615,007, 2,615,008, B. 8. 0 2. 0 150 28 B- . 8. 0 2.0 4 150 21 2,582,985 and 2,581,464, by the condensation of varying B _ . 9. 0 1. 0 0 150 35 proportions of epichlorhydrin to bisphenol or polyhydric B. _ . 9. 0 1. 0 0. 4 150 13 G- _ 8. 0 2. 0 ' 0 ‘ 150 36 alcohol and subsequent dehydrohalogenation with sodium C. _ B. 0 2. 0 0. 4 150 20 hydroxide. The table which follows indicates the‘ ratio C- . 9. 0 l. 0 0 150 57 O. _ 0. 0 1. 0 0. 4 150 24 of epichlorhydrin to bisphenol or alcohol used to prepare E - 8. 0 2. 0 0 150 14 the glycidyl polyethers. In the examples and tables which E _ 8. 0 2. 0 0. 4 150 I 9 E _ 9. 0 . 1. 0 U 150 40 follow, BTMACl will be used instead of benzyltrimethyl E _ 9. 0 1. 0 0. 4 150 20 ammonium chloride and the polyepoxides will be referred F. __ 8. 0 2. 0 0 150 21 F. .._ 8.0 2. 0 0. 4 150 3 8 to as Epoxide A, B, C, etc. Thus, Epoxidc A is made F- __ 9. 0 1. 0 0 100 184 from 1.0 mol of bisphenol and 10.0 mols of epichlor F ............. -- 9. 0 1. 0 0. 4 150 20 hydrin, and has an epoxide equivalent‘of 190. 15 1 BTMACl represents benzyltrimethyl ammonium chloride (60 per TABLE OF EPOXIDES cent aqueous solution). 9 Became exceedingly exothermic. , M01 ratio Example 2 . Epoxide Epoxlde Hydroxyl compound , Equiv Epichlor- Hydroxyl alent In a beaker, 9.0 grams of Epoxide B and 1.0 gram of hydrin Com 20 dicyandiamide are heated with stirring at 170° C. until pound a homogeneous melt is obtained. Into the melt is blended 0.4 gram of a sixty percent aqueous solution of benzyl 10.0 1; 0 190 trimethyl ammonium chloride after which the mixture is B 2. 04 1.0 340 ..do-__ 1. 21 1. 0 960 poured into an aluminum cup and is heated in a 150° C. D Trimethylol propane- 2. 0 1. 0 172 oven.
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