Resin compositions
View Patent ↗Compositions comprising unsaturated resin and catalyst comprising transition metal, such as a complex of ligands and transition metals. The compositions may further comprise filler or rheology modifiers.
1. A composition comprising a resin having ethylenic unsaturation, a filler in the amount of about 10% to about 250% by weight of the resin, and a catalyst comprising either a complex of a transition metal and a ligand or ferric acetoacetonate wherein the ligand comprises a structure
wherein, each R is independently selected from: hydrogen, F, Cl, Br, hydroxyl, C 1 -C 4 -alkylO—, —NH—CO—H, —NH—CO—C 1 -C 4 -alkyl, —NH 2 , —NH—C 1 -C 4 -alkyl, and C 1 -C 4 -alkyl;
R1 and R2 are independently selected from: C 1 -C 4 -alkyl, C 6 -C 10 -aryl, and, a group containing a heteroatom capable of coordinating to a transition metal wherein at least one of R1 and R2 is the group containing the heteroatom and the transition metal is selected from the group consisting of manganese in oxidation states II-V, iron in oxidation states II-V, copper in oxidation states I-III, cobalt in oxidation states I-III, titanium in oxidation states II-IV, tungsten in oxidation states IV-VI, vanadium in oxidation states II-V, molybdenum in oxidation states II-VI and combinations thereof;
R3 and R4 are independently selected from hydrogen, C 1 -C 8 alkyl, C 1 -C 8 -alkyl-O—C 1 -C 8 -alkyl, C 1 -C 8 -alkyl-O—C 6 -C 10 -aryl, C 6 -C 10 -aryl, C 1 -C 8 -hydroxyalkyl, and —(CH 2 ) n C(O)OR 5 and R5 is independently selected from hydrogen, C 1 -C 6 -alkyl and mixtures thereof and n is from 0 to 4;
X is selected from C═O, —[C(R6) 2 ] y — wherein Y is from 0 to 3 and each R6 is independently selected from hydrogen, hydroxyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkyl; and wherein said composition further comprises a co-promoter selected from the group consisting of 2,4-pentanedione, 2-acetylbutyrolactone, ethyl acetoacetonate, n,n-diethyl acetoacetamide and combinations thereof.
2. The composition of claim 1 wherein resin having ethylenic unsaturation has an acid value of about 5 to about 40.
3. The composition of claim 1 wherein the resin having ethylenic unsaturation is an unsaturated polyester resin or a vinyl ester resin.
4. The composition of claim 1 wherein the filler is selected from the group consisting of aluminum trihydroxide, calcium carbonate, talc and combinations thereof.
5. The composition of claim 1 comprising about 50% to about 200% filler by weight of the resin.
6. The composition of claim 1 comprising about 0.01% to about 0.25% catalyst by weight of the resin.
7. The composition of claim 1 further comprising a dispersing agent.
8. The composition of claim 7 wherein the dispersing agent comprises copolymers having an acidic functional group, unsaturated polycarboxylic polymer comprising polysiloxane copolymer or alkylol ammonium salt of an acidic polyester.
9. The composition of claim 7 wherein the dispersing agent is present in an amount of about 0.1% to about 3% by weight of the resin.
10. The composition of claim 1 further comprising a rheology modifier selected from the group consisting of fumed silica, organic clay and combinations thereof.
11. The composition of claim 1 further comprising polysorbate 20, polyhydroxycarboxylic acid esters and combinations thereof.
12. A composition comprising a resin having ethylenic unsaturation, a rheology modifier and a catalyst comprising either a complex of a transition metal and a ligand or ferric acetoacetonate wherein the ligand comprises a structure
wherein, each R is independently selected from: hydrogen, F, Cl, Br, hydroxyl, C 1 -C 4 -alkylO—, —NH—CO—H, —NH—CO—C 1 -C 4 -alkyl, —NH 2 , —NH—C 1 -C 4 -alkyl, and C 1 -C 4 -alkyl;
R1 and R2 are independently selected from: C 1 -C 4 -alkyl, C 6 -C 10 -aryl, and, a group containing a heteroatom capable of coordinating to a transition metal wherein at least one of R1 and R2 is the group containing the heteroatom and the transition metal is selected from the group consisting of manganese in oxidation states II-V, iron in oxidation states II-V, copper in oxidation states I-III, cobalt in oxidation states I-III, titanium in oxidation states II-IV, tungsten in oxidation states IV-VI, vanadium in oxidation states II-V, molybdenum in oxidation states II-VI and combinations thereof;
R3 and R4 are independently selected from hydrogen, C 1 -C 8 alkyl, C 1 -C 8 -alkyl-O—C 1 -C 8 -alkyl, C 1 -C 8 -alkyl-O—C 6 -C 10 -aryl, C 6 -C 10 -aryl, C 1 -C 8 -hydroxyalkyl, and —(CH 2 ) n C(O)OR 5 and R5 is independently selected from hydrogen, C 1 -C 6 -alkyl and mixtures thereof and n is from 0 to 4;
X is selected from C═O, —[C(R6) 2 ] y — wherein Y is from 0 to 3 and each R6 is independently selected from hydrogen, hydroxyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkyl; and wherein said composition further comprises a co-promoter selected from the group consisting of 2,4-pentanedione, 2-acetylbutyrolactone, ethyl acetoacetonate, n,n-diethyl acetoacetamide and combinations thereof.
13. The composition of claim 12 wherein the rheology modifier is selected from the group consisting of fumed silica, organic clay and combinations thereof.
14. The composition of claim 12 wherein the resin having ethylenic unsaturation is an unsaturated polyester resin or a vinyl ester resin.
15. The composition of claim 12 comprising about 0.01% to about 0.25% catalyst by weight of the resin.