FIELD: chemistry.
SUBSTANCE: invention relates to a method of producing isosorbide di(meth)acrylate via re-esterification of alkyl(meth)acrylate with isosorbide. Method of producing isosorbide di(meth)acrylate used as a resin component of two-component adhesive compositions by re-esterification of alkyl(meth)acrylate with 1–4 carbon atoms in alkyl isosorbide involves steps of: (i) reacting alkyl(meth)acrylate with isosorbide in the presence of a titanium (IV) or zirconium (IV)-containing catalyst and stabilizer, as well as in the presence of an azeotropic agent which is an alkyl(meth)acrylate with 1–4 carbon atoms in alkyl, forming an azeotropic mixture containing alkyl(meth)acrylate and formed alcohol, (ii) continuous distillation of an azeotropic mixture consisting of an azeotrope-forming agent and alcohol, wherein steps (i) and (ii) are simultaneously realized until substantially complete conversion of isosorbide is achieved, to form a mixture of products containing titanium (IV) or zirconium (IV)-containing catalyst, unconverted alkyl(meth)acrylate and azeotrope-forming agent, (iii) adding water to the product obtained in steps (i) and (ii) containing di(meth)acrylate isosorbide, and separating the product of hydrolysis of titanium (IV) or zirconium (IV) of the catalyst, (iv) distilling unconverted alkyl(meth)acrylate and an azeotrope-forming agent from the mixture of products, (v) distilling water from the mixture of products, wherein step (iv) can also be carried out before step (iii), and steps (iv) and (v) can perform also at a single stage of distillation. Isosorbide di(meth)acrylate obtained using said method as a resin component of two-component adhesive compositions is used. Two-component adhesive composition includes: (i) a synthetic resin with viscosity at 23 °C in range from 100 to 10,000 MPa⋅c, which contains isosorbide di(meth)acrylate obtained using said method, and (ii) a curing agent for synthetic resin.
EFFECT: technical result is isosorbide di(meth)acrylate by re-esterification of alkyl(meth)acrylate with isosorbide with high yield of isosorbide di(meth)acrylate with high degree of purity, wherein by-products are formed only in insignificant amounts.
11 cl, 4 ex
Authors
Dates
2019-10-17—Published
2016-02-24—Filed