Divinylarene dioxide resin compositions
A curable divinylarene dioxide resin composition including (a) at least one divinylarene dioxide, and (b) at least one diphenol curing agent; a process for making the curable divinylarene dioxide resin composition; and a cured divinylarene dioxide resin composition made therefrom. The cured product made from the above curable divinylarene dioxide resin composition offers improved properties such as lower viscosity and a high heat resistance compared to known cured products prepared from known epoxy resins.
1. A curable divinylarene dioxide resin composition comprising:
(a) at least one divinylarene dioxide,
(b) at least one diphenol curing agent, and
(c) a curing catalyst selected from the group consisting of imidazoles, quaternary ammonium halides and carboxylates, quaternary phosphonium halides and carboxylates, and mixtures thereof;
wherein a concentration of the diphenol curing agent, as an equivalent ratio r of epoxide groups to a total of phenolic groups of the diphenol curing agent, ranges from 1.2 to 2; and
wherein the curable divinylarene dioxide resin composition, upon being cured, forms a cured epoxy resin which: (1) exhibits a heat resistance, as determined by glass transition temperature greater than a corresponding composition lacking a curing catalyst, component (c); and (2) is insoluble in an organic solvent.
2. The composition of claim 1 , wherein the divinylarene dioxide is selected from the group consisting of divinylbenzene dioxide, divinylnaphthalene dioxide, divinylbiphenyl dioxide, divinyldiphenylether dioxide, and mixtures thereof.
3. The composition of claim 1 , wherein the divinylarene dioxide is divinylbenzene dioxide.
4. The composition of claim 1 , wherein the concentration of said divinylarene dioxide ranges from about 10 weight percent to about 90 weight percent.
5. The composition of claim 1 , wherein the at least one diphenol curing agent comprises a diphenol, a bisphenol, or a difunctional phenolic oligomer.
6. The composition of claim 1 , including a monophenol selected from the group consisting of phenol; o-, m-, or p-cresol; p-tert-butylphenol; m-chlorophenol; anisole; p-phenylphenol; 4-hydroxydiphenylether; 1- or 2-naphthol; and mixtures thereof.
7. The composition of claim 6 , wherein the concentration of said monophenol ranges from about 0.01 weight percent to about 50 weight percent.
8. The composition of claim 1 , wherein the concentration of said catalyst ranges from about 0.01 weight percent to about 20 weight percent.
9. The composition of claim 1 , including a co-curing agent.
10. A thermoset cured product prepared by curing the composition of claim 1 , wherein the cured product comprises a coating, an adhesive, a composite or a laminate.
11. A process for preparing a curable divinylarene dioxide resin composition comprising admixing:
(a) at least one divinylarene dioxide resin;
(b) at least one diphenol curing agent; and
(c) a curing catalyst selected from the group consisting of imidazoles, quaternary ammonium halides and carboxylates, quaternary phosphonium halides and carboxylates, and mixtures thereof;
wherein a concentration of the diphenol curing agent, as an equivalent ratio r of epoxide groups to a total of phenolic groups of the diphenol curing agent, ranges from 1.2 to 2; and
wherein the curable divinylarene dioxide resin composition, upon being cured, forms a cured epoxy resin which: (1) exhibits a heat resistance, as determined by glass transition temperature greater than a corresponding composition lacking a curing catalyst, component (c); and (2) is insoluble in an organic solvent.
12. A process for preparing a cured thermoset comprising:
(i) preparing a curable divinylarene dioxide resin composition comprising admixing:
(a) at least one divinylarene dioxide resin;
(b) at least one diphenol curing agent; and
(c) a curing catalyst selected from the group consisting of imidazoles, quaternary ammonium halides and carboxylates, quaternary phosphonium halides and carboxylates, and mixtures thereof;
wherein a concentration of the diphenol curing agent, as an equivalent ratio r of epoxide groups to a total of phenolic groups of the diphenol curing agent, ranges from 1.2 to 2 and
wherein the curable divinylarene dioxide resin composition, upon being cured, forms a cured epoxy resin which: (1) exhibits a heat resistance, as determined by glass transition temperature greater than a corresponding composition lacking a curing catalyst, component (c); and (2) is insoluble in an organic solvent; and
(ii) heating the composition of step (i) at a temperature of from about 25° C. to about 300° C.