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United States Patent Office 3,663,599 United States Patent Office Patented May 16, 1972 2 3,663,599 Cia-CH-Y METHOD OF PRODUCING WINYLC (3) POLYMERIZABLE MONOMERS Masamitsu Koshimura, Tokyo, Yukinori Haruta and Junichi Matsuzaka, Yokohama, and Shinichi Wako, 5 wherein Y is hydrogen, methyl, phenyl or CHZ group (Z. Fujisawa, Japan, assignors to Nippon Oils and Fats is halogen or alkyl group) Company Limited, Tokyo, Japan No Drawing. Filed May 6, 1969, Ser. No. 822,299 X Y Y Claims priority, application Japan, May 8, 1968, CH=(-COOCH-CHOOCR coo). CH-CH-OH (4) 43/30,658; Oct. 15, 1968, 43/75,082; Nov. 5, O 1968, 43/80,376 wherein X, Y and R have the same meanings as described at C. C07e 69/80 above, provided that when two or more Y and R groups U.S. C. 260-475 P 9 Claims are contained in one molecule, Y and R may be same or different groups, that is, they may be mixture systems and n is an integer of 1 to 3. ABSTRACT OF THE DISCLOSURE 5 In this case, the ring breakage of the monoepoxy com Reactive monomeric polyester containing a vinylic un pound mainly occurs according to the following Formula saturated bond and a hydroxyl group, which has the foll 5 and therefore, the products are shown by the above lowing general formula Formula 4, but the ring breakage as shown in the follow ing Formula 6 probably occurs somewhat and consequent * Y Y ly the products obtained in the present invention may be CH-C-COO(CH-CH-O OC-RCOO). CH-CH-OH a mixture of the products having the following Formulae wherein X is hydrogen, methyl or ethyl group, Y is 7 and 8, wherein the position of carbon to be bonded with hydrogen, methyl, phenyl or CHZ group, in which Z Y varies. Accordingly, although in the above Formula 4, is a halogen or an alkyl group, R represents an aliphatic, the right end is shown by hydroxyl group of the secondary alicyclic or aromatic group and n is an integer of 1 to 3, 25 alcohol, the product having hydroxyl group of the pri is produced by reacting in one step at least one vinylic mary alcohol as shown in the following Formula 8 is unsaturated acid having the general formula naturally mixed and the expression of the above Formula 4 of the products means also the mixture of such products Y having the Formulae 7 and 8. CH-C-C O OE 30 with at least one organic dibasic acid anhydride having ?H-CH-Y the general formula ()- (5) CO 35 R^ Yo CH-6H-Y Yo6 ()- (6) and at least one monoepoxide having the general formula aCOO CE-COOC-R- 40 CH-C-Y y (7) -R COO C-CH-OH y (8) X, Y and R in the above formula having the same mean ings as described above, at a temperature lower than 100 45 C. by using lithium salt alone or in admixture with quat In general, it has been known that an initiator, a dibasic ernary ammonium salt as a catalyst. acid anhydride (abridged as acid anhydride hereinafter) and a monoepoxy compound take place polyesterification. oasis Englia reaction at a high temperature of 130 to 150° C. in the The present invention relates to novel vinylic polym 50 absence of a catalyst, and the reactivity decreases rapidly erizable monomers and a method of producing said mono at a temperature lower than such a temperature. In this mers, more particularly, production of reactive monomers invention, when the reaction for producing the product having vinylic unsaturated group as shown in the follow having the above described Formula 4 is carried out, it is ing Formula 4 by reacting vinylic unsaturated acid(s) desirable to effect the reaction at a temperature lower (initiator(s) having the following Formula 1, as an 55 than 100 C. in order not to polymerize the vinyl group. organic dibasic acid anhydride(s) having the following Because the reaction system contains acrylic acid, meth Formula 2 and monoepoxy compound(s) having the acrylic acid or ox-ethyl acrylic acid (abridged these acids following Formula 3 in the presence of lithium salt as de as the vinyl unsaturated acid), which is readily polymer fined hereinafter as a catalyst without causing thermal ized rapidly at a temperature higher than 100° C. polymerization of the unsaturated group in the vinylic 60 On the other hand, in case of absence of catalyst the reaction velocity is very slow and the reaction does not unsaturated acid. substantially proceed and consequently, the reaction of X the present invention needs a catalyst which can cause CH-C-COO (1) the esterification reaction at a temperature lower than 65 100° C. After many investigations the inventors have wherein X is hydrogen, methyl or ethyl group. found that lithium salt can promote the reaction effec tively at relatively lower temperature and have succeeded CO in production of high quality of monomeric polyesters R^ So having the above Formula 4 in a high yield. Yo O (2) 70 Such products, when n is large are considered to be sorts of polyesters in structure, but in view of presence wherein R is an aliphatic, alicyclic or aromatic group. of the vinylic unSaturated group in the molecule they are 3,663,599 3 4. considered to be monomers, therefore they are referred a second ester and in the third step the second ester hav to as "monomer' hereinafter. ing a terminal carboxyl group is reacted with a mono The monomers of the present invention can be used epoxy compound to form the object product having the in various fields by utilizing the reactivity of the vinyl above Formula 4. However, according to the method group and the functional group (terminal hydroxyl group) of the present invention it is possible to obtain the object present in the molecule. Namely, the monomers can be product having the above Formula 4 in one step, from copolymerized with the other comonomers containing the vinylic unsaturated acid, the acid anhydride and the polymerizable unsaturated groups, such as, styrene, meth monoepoxy compound. Therefore the present invention acrylates, acrylates, acrylonitriles, butadiene, vinyl ace is very advantageous. Furthermore, in this invention, the tate, etc., and further, can form cross-linkage by utilizing O value of n in the configuration of the Formula 4 can be the functional group, for example, can form cross-linkage controlled as described below, by the feeding ratio of the through a reaction of the terminal hydroxyl group with above described three starting materials. With respect to polyisocyanate and the like. Moreover, the monomers one mole of vinylic unsaturated acid, when the acid can be used for thermoplastic molding, film, sheet, fila anhydride is 1 mole and the epoxy compound is 2 moles, ment and the like and are useful broadly in the same the monomer wherein in is 1 can be obtained, when the field as the thermosetting plastics and provide new ma acid anhydride is 2 moles and the monoepoxy compound terial in a field of high molecular weight compound. is 3 moles, the monomer wherein in is 2 can be obtaincd Furthermore, the monomers can be used for an improver and when the acid anhydride is 3 moles and the mono of plastics, synthetic fiber, film and sheet or for main epoxy compound is 4 moles, the monomer wherein n is component. 20 3 can be obtained. In practice, the amount of the mono The first merit of the invention consists in that the epoxy compound added is somewhat larger than the cal monomers can be produced at a temperature lower than culated amount based on the reason as described herein 100° C. without causing thermal polymerization of the after. In case of preparing in of 4 or more, it is rather vinyl group by using the catalyst according to the present difficult to promote the esterification reaction, because invention and the reaction velocity is same as or higher 25 of the viscosity in the reaction and the state of starting than that at a high temperature in the absence of catalyst. materials. And further, such monomers have no particu Furthermore, when using some catalyst, if the reaction lar advantage in view of the utilization and properties proceeds to some extent, the reaction reaches equilibrium as compared with the monomers, wherein n is 3, and are and the progress of the reaction stops, while according not valuable. to the catalyst of the present invention, the reaction ratio 30 The fifth merit is attained when a lithium salt of vinylic is very high and a reaction percentage of more than 98% unsaturated acid corresponding to vinylic unsaturated acid can be fairly easily attained. to be used as one component of the starting materials The second merit consists in that the catalyst added is used as the reaction catalyst. For example, when acrylic in the reaction precipitates again at the end of the reac acid is one component of the starting materials, lithium tion and after completed the reaction, a major part of acrylate is used as the catalyst. In the reaction of the the catalytic component in the reaction product can be present invention, when any other lithium salt than such removed by only a filtration of the reaction product and lithium salts is used as the catalyst, the negative group consequently, an amount of the catalytic component re bonded to lithium in the lithium compound is separated mained in the reaction product is very small and such in the reaction from lithium and reacts with the mono an amount is not problem in practice.
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