Monomer with anti-microbial character, polymer using the same, and manufacturing method thereof
The present invention relates to a monomer with anti-microbial characteristics, a polymeric compound with anti-microbial characteristics using the same, and manufacturing methods thereof, and more particularly, to an antimicrobial monomer comprising a saturated hydrocarbon having a polymerizable functional group within its structure. Also, the present invention provides a polymeric compound using the above antimicrobial monomer, a manufacturing method thereof, and a polymeric resin composition. The compounds according to the present invention have durable antimicrobial activity and high heat resistance, they do not give rise to toxicity when added to conventional resins by not eluting the antimicrobial compounds, and they do not have an effect on the properties of molded products.
1. An antimicrobial acrylic copolymer having an average molecular weight of 10,000˜1,000,000, represented by the following formula 10:
wherein
R 12 and R 13 are each independently or simultaneously hydrogen or a methyl group;
R 14 is a C 1 ˜C 18 alkyl group comprising one or more selected from the group consisting of ester, carbonyl, amide, amine, cycloalkyl, ether, hydroxy, carboxylic acid, C 2 ˜C 10 hetero ring containing N or O, sulfonyl, silane, lactone, and aldehyde groups;
m and n are each an integer greater than zero satisfying said molecular weight; and
X is a compound of the following formula 2a:
wherein R 1 and R 2 are each independently or simultaneously hydrogen, a halogen atom, an amine, or a C 1 ˜C 20 alkyl group; R 3 and R 4 are each independently or simultaneously hydrogen, a hydroxy group, a C 1 ˜C 20 alkoxide, a halogen atom, or a C 1 ˜C 20 alkyl group; R 5 is hydrogen, a C 1 ˜C 20 alkyl, a cyclopropyl, or an aromatic C 1 ˜C 20 hydrocarbon; R 6 is hydrogen, sodium, potassium, or a C 1 ˜C 150 alkyl group that comprises or does not comprise a polymerizable functional group; R 8 , R 9 , and R 10 are each independently or simultaneously carbon or nitrogen; and R 11 is hydrogen, an amine (1°, 2°, 3°), a halogen atom, or a C 1 ˜C 20 alkyl group.
2. A method of manufacturing the antimicrobial acrylic copolymer of formula 10 of claim 1 , comprising the step of radically polymerizing a compound of the following formula 11:
wherein R 12 is hydrogen or a methyl group, and
wherein X is a compound of the following formula 2a
with a compound of the following formula 12:
wherein R 13 is hydrogen or a methyl group, and
R 14 is a C 1 ˜C 18 alkyl group comprising one or more selected from the group consisting of ester, carbonyl, amide, amine, cycloalkyl, ether, hydroxy, carboxylic acid, C 2 ˜C 10 hetero ring containing N or O, sulfonyl, silane, lactone, and aldehyde groups.
3. The method of the antimicrobial acrylic copolymer of claim 2 , characterized in that said compound of formula 12 is an acrylic monomer consisting of a hydrocarbon main chain attributed to a vinyl alcohol, acrylonitrile, butadiene, acrylic acid, styrene, acrylimide, methylmethacrylic acid, methacrylic acid, vinylchloride, vinylfluoride, or vinylacetateacrylic acid as a main chain.