Latex functionalized with phosphorus acid and photoinitiator groups
The present invention is a composition comprising a stable aqueous dispersion of polymer particles comprising structural units of a phosphorus acid monomer or a salt thereof and structural units of a photoinitiator monomer. Gloss retention of paints containing the latex described herein is markedly improved over paints that do not have photoinitiator chemically bound to the latex particles.
1. A composition comprising a stable aqueous dispersion of polymer particles comprising structural units of a phosphorus acid monomer or a salt thereof and structural units of a photoinitiator monomer represented by either of the following formulas:
where j is 0, 1, 2, or 3; and k is 0, 1, or 2;
each R 1 and R 2 are independently C 1 -C 6 -alkyl, CF 3 , OH, NH 2 , COOH, or COOCH 3 ; or R 1 and R 2 , together with the carbon atom to which they are attached, form a bridging S, O, NH, or N—CH 3 group;
each R 3 is independently CF 3 , C 1 -C 6 -alkyl, —O—C 1 -C 6 -alkyl, —COO—C 1 -C 6 -alkyl, halo, CN, COOH, or OH;
X is C 1 -C 6 -alkyl;
Y is an organic hydrocarbon-containing radical optionally comprising at least one O, N, or S heteroatom, which radical further comprises an unsaturated substituent that is copolymerizable with an acrylic, methacrylic, styrene, or vinyl ester monomer; and
Z is an acrylate or methacrylate functionalized group;
wherein the concentration of structural units of the phosphorus acid monomer or salt thereof is in the range of from 0.2 to 5 weight percent, based on the weight of the polymer particles; and the concentration of structural units of the photoinitiator monomer is in the range of from 0.05 to 10 weight percent, based on the weight of the polymer particles.
2. The composition of claim 1 wherein the photoinitiator monomer is selected from the group consisting of 2-hydroxy-3-(methacryloyloxy)propyl 2-benzoylbenzoate; 2-(((4-benzoylphenoxy)carbonyl)amino)ethyl methacrylate; 2-(acryloyloxy)-3-((9-oxo-9H-thioxanthen-2-yl)oxy)propyl methacrylate; 2-(2-(4-benzoyl-2,5-dimethylphenoxy)ethoxy)ethyl methacrylate; 2-(methacryloyloxy)ethyl 4-(4-chlorobenzoyl)benzoate; and 4-benzoylphenyl methacrylate.
3. The composition of claim 2 wherein the polymer particles comprise from 0.8 to 2 weight percent structural units of phosphoethyl methacrylate and from 0.2 to 5 weight percent structural units of the photoinitiator monomer, based on the weight of the polymer particles, wherein the photoinitiator monomer is 2-hydroxy-3-(methacryloyloxy)propyl 2-benzoylbenzoate.
4. The composition of claim 3 wherein the polymer particles further comprise 40 to 50 weight percent structural units of methyl methacrylate or styrene; from 15 to 25 weight percent structural units of butyl acrylate, from 23 to 33 weight percent structural units of 2-ethylhexyl acrylate; from 0.05 to 2 weight percent structural units of methacrylic acid or a salt thereof.
5. The composition of claim 4 wherein the polymer particles further comprise from 0.1 to 5 weight percent structural units of ureido methacrylate, based on the weight of the polymer particles.
6. The composition of claim 1 wherein the phosphorus acid monomer or salt thereof is phosphoethyl methacrylate or a salt thereof.
7. The composition of claim 6 wherein the polymer particles comprise from 0.5 to 3 weight percent structural units of phosphoethyl methacrylate or a salt thereof, based on the weight of the polymer particles.