Flame retardant for epoxy resin containing phosphonate and phosphinate functionality
There is provided herein a curing agent compound for curing thermosetting resins, e.g., epoxy resins, a composition comprising a thermoplastic and/or thermosetting resin, e.g., an epoxy resin and the curing agent, an article comprising the curing agent, and a method of making the curing agent.
1. A compound having the general formula (I):
wherein each R is independently selected from H; —OH; an alkyl containing from 1 to about 8 carbon atoms;
where R* is an alkyl group containing from 1 to 8 carbon atoms or a substituted or unsubstituted phenyl;
a phosphinate moiety of the formula (II):
wherein R 1 is a divalent linear or branched alkylene moiety of from 1 to 3 carbon atoms, and the dashed line represents a bond to the structure of formula (I) above;
a phosphonate moiety of the general formula (III):
and,
a substituted aryl moiety of the general formula (IV):
where R 2 is a divalent linear or branched alkylene moiety of from 1 to 4 carbon atoms, and the dashed line represents a bond to the structure of formula (I) above, and R 3 is defined the same as R except that R 3 cannot be the substituted aryl moiety of the general formula (IV) and at least one R 3 is a group of the formula (II);
and provided that the number of R groups of the formula (I) which are of the formula (II) are 1 or 2, the number of R groups of the formula (I) which are of the formula (III) are 1 or 2 and provided that none of the R groups or only one of the R groups of formula (I) are of the formula (IV) and further provided that when none of the R groups of the formula (I) are of the formula (IV), then the total number of R groups which are of the formula (II) and (III) can be up to 4, and if one of the R groups of the formula (I) is of the formula (IV) then the total number of R groups which are of the formula (II), (III) and (IV) are up to four.
2. The compound of claim 1 wherein the compound is selected from the fomulae (V)-(XI):
3. A composition comprising a thermosetting resin, from about 10 to about 150 parts by weight of the compound of claim 1 of formula (I) per 100 parts of the thermosetting resin, and optionally one or more of a co-crosslinker, a curing catalyst, a Lewis acid, a benzooxazine-containing compound, and optionally an inhibitor.
4. The composition of claim 3 wherein the thermosetting resin is an epoxy resin.
5. The composition of claim 3 wherein the thermosetting resin is selected from the group consisting of epoxy, polyurethane, polyisocyanates, benzoxazine ring-containing compounds, unsaturated resin systems containing double or triple bonds, polycyanate ester, bismaleimide, triazine, bismaleimide and mixtures thereof.
6. A composition comprising a thermoplastic resin, from about 10 to about 150 parts by weight of the compound of claim 1 of formula (I) per 100 parts by weight of thermoplastic resin, and optionally a co-crosslinker, optionally a Lewis acid, optionally a benzooxazine-containing compound, and optionally an inhibitor.
7. A composition comprising a thermoplastic resin, a thermosetting resin, from about 10 to about 150 parts by weight of the compound of claim 1 of formula (I) per 100 parts by weight of the combined weight of thermoplastic resin and thermosetting resin, and optionally a co-crosslinker, optionally a curing catalyst, optionally a Lewis acid, optionally a benzooxazine-containing compound, and optionally an inhibitor.
8. The composition of claim 3 wherein the compound of formula (I) is in the absence of halogen.
9. The composition of claim 3 formulated as any one of a coating formulation, an encapsulant, a composite, an adhesive, a molding a bonding sheet or a laminated plate.
10. An article comprising the composition of claim 3 .
11. The article of claim 10 wherein said article can be used in lead free soldering applications and electronic devices.
12. The article of claim 10 wherein the article further comprises a copper foil.
13. The article of claim 12 wherein said article is a printed wiring board.
14. A prepreg comprising the composition of claim 3 .
15. A laminate or a bonding sheet comprising the composition of claim 3 .
16. A printed wiring board comprising prepreg of claim 14 .
17. A printed wiring board comprising the laminate of claim 15 .
18. A process of making a laminate that contains the composition of claim 3 comprising impregnating the composition into a filler material, to form a prepreg, followed by processing the prepreg at elevated temperature to promote partial cure to a B-stage and then laminating two or more of said prepregs at elevated pressure and temperature to form a laminate.
19. A printed wiring board made by the process of claim 18 .